(2S,3S,4aR,5S,6R,8aR,2'R,3'R)-6-(3',4'-dibenzyloxy-2'-methylbutyl)-2,3-dimethoxy-5-methoxymethoxy-2,3-dimethyl-2,3,4a,5,6,8a-hexahydrobenzo[1,4]dioxine

Base Information

Chemical Name:(2S,3S,4aR,5S,6R,8aR,2'R,3'R)-6-(3',4'-dibenzyloxy-2'-methylbutyl)-2,3-dimethoxy-5-methoxymethoxy-2,3-dimethyl-2,3,4a,5,6,8a-hexahydrobenzo[1,4]dioxine
CAS No.:856191-00-9
Molecular Formula:C₃₃H₄₆O₈
Molecular Weight:570.723
Hs Code.:

Synonyms:(2S,3S,4aR,5S,6R,8aR,2'R,3'R)-6-(3',4'-dibenzyloxy-2'-methylbutyl)-2,3-dimethoxy-5-methoxymethoxy-2,3-dimethyl-2,3,4a,5,6,8a-hexahydrobenzo[1,4]dioxine

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Chemical Property of (2S,3S,4aR,5S,6R,8aR,2'R,3'R)-6-(3',4'-dibenzyloxy-2'-methylbutyl)-2,3-dimethoxy-5-methoxymethoxy-2,3-dimethyl-2,3,4a,5,6,8a-hexahydrobenzo[1,4]dioxine

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Technology Process of (2S,3S,4aR,5S,6R,8aR,2'R,3'R)-6-(3',4'-dibenzyloxy-2'-methylbutyl)-2,3-dimethoxy-5-methoxymethoxy-2,3-dimethyl-2,3,4a,5,6,8a-hexahydrobenzo[1,4]dioxine

There total 8 articles about (2S,3S,4aR,5S,6R,8aR,2'R,3'R)-6-(3',4'-dibenzyloxy-2'-methylbutyl)-2,3-dimethoxy-5-methoxymethoxy-2,3-dimethyl-2,3,4a,5,6,8a-hexahydrobenzo[1,4]dioxine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 89.0%

: 856190-76-6
(2S,3S,5R,6R,1'S,2'R,2''R,3''R)-5-[2'-(3'',4''-bis(benzyloxy)-2''-methylbutyl)-1'-methoxymethoxybut-3'-enyl]-2,3-dimethoxy-2,3-dimethyl-6-vinyl[1,4]dioxane

: 856191-00-9
(2S,3S,4aR,5S,6R,8aR,2'R,3'R)-6-(3',4'-dibenzyloxy-2'-methylbutyl)-2,3-dimethoxy-5-methoxymethoxy-2,3-dimethyl-2,3,4a,5,6,8a-hexahydrobenzo[1,4]dioxine

Guidance literature:: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In toluene; for 1h; Heating;
DOI:10.1002/anie.200500174

Reference yield:

: (2S,3R,5S,6S,1'S,2'R,2''R,3''R)-3-[2'-(3'',4''-bis(benzyloxy)-2''-methylbutyl)-1'-methoxymethoxybut-3'-enyl]-5,6-dimethoxy-5,6-dimethyl[1,4]dioxane-2-carbaldehyde

: 856191-00-9
(2S,3S,4aR,5S,6R,8aR,2'R,3'R)-6-(3',4'-dibenzyloxy-2'-methylbutyl)-2,3-dimethoxy-5-methoxymethoxy-2,3-dimethyl-2,3,4a,5,6,8a-hexahydrobenzo[1,4]dioxine

Guidance literature:: Multi-step reaction with 2 steps

1: 87 percent / n-BuLi / hexane; tetrahydrofuran / 12 h / -78 - 20 °C

2: 89 percent / (1,3-Mes₂-2-imidazolidinylidene)Ru=CHPhCl₂(Cy₃P) / toluene / 1 h / Heating

With n-butyllithium; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; hexane; toluene; 1: Wittig olefination;
DOI:10.1002/anie.200500174

Reference yield:

: 856190-83-5
(2R,3R,5S,6S,1'S,2'R,2''R,3''R)-{3-[2'-(3'',4''-bis(benzyloxy)-2''-methylbutyl)-1'-methoxymethoxybut-3'-enyl]-5,6-dimethoxy-5,6-dimethyl[1,4]dioxan-2-yl}methanol

: 856191-00-9
(2S,3S,4aR,5S,6R,8aR,2'R,3'R)-6-(3',4'-dibenzyloxy-2'-methylbutyl)-2,3-dimethoxy-5-methoxymethoxy-2,3-dimethyl-2,3,4a,5,6,8a-hexahydrobenzo[1,4]dioxine

Guidance literature:: Multi-step reaction with 3 steps

1: DMSO; oxalyl chloride; Et₃N / CH₂Cl₂ / -78 - 20 °C

2: 87 percent / n-BuLi / hexane; tetrahydrofuran / 12 h / -78 - 20 °C

3: 89 percent / (1,3-Mes₂-2-imidazolidinylidene)Ru=CHPhCl₂(Cy₃P) / toluene / 1 h / Heating

With n-butyllithium; oxalyl dichloride; dimethyl sulfoxide; triethylamine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; hexane; dichloromethane; toluene; 1: Swern oxidation / 2: Wittig olefination;
DOI:10.1002/anie.200500174